Triacetoxyperiodinane → HCID 59253148, compound

Participants

Reaction Steps

Dess-Martin periodinane (950 g, 2.24 mmol) is added to a solution of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (600 mg, 1.60 mmol) (see Amide Method B1 or B2) in DCM (10 mL). The reaction mixture is stirred at room temperature for 40 minutes. After this time, the reaction mixture is quenched with 50 mL (1:1) saturated aqueous NaHCO3 solution and saturated aqueous sodium thiosulfate solution and stirred at room temperature for 3 h then extracted with DCM 3 times. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. Yield: quantitative. 1H NMR (400 MHz, DMSO-d) δ ppm 1.4 (6H, s), 1.65 (2H, m), 1.7 (6H, s), 1.8 (2H, m), 3.4 (2H, m), 3.9 (3H, m), 6.4 (1H, s), 9.6 (1H, s), 11.5 (1H, s).

Provenance & Evidence